Match Makers
by Caitlinrosee
Summary: Salesman Killian Jones has been in love with receptionist Emma Swan for as long as he can remember. While he's left pining away for her, a ring on her finger from another man, he's setting up half the office on dates. (In other words, OUAT in an Office 'verse)
1. Chapter 1

Killian Jones had been in love with Emma Swan since before he could remember.

Which meant he'd been working at this job for _far_ too long. _Storybrooke Paper Company_ was supposed to be a temporary thing. He was supposed to sell some paper, save up, and get out. But it had been three long years and here he was, still at the same desk, with the same crabby deskmate.

In love with the same - _engaged_ \- receptionist.

Killian started at SPC shortly before the engagement. Emma had been the first person to greet him - natural, with a title like _reception_ ist and a desk by the front door. But then she'd been essentially the only person to greet him, aside from his overzealous, well-meaning boss, Regina.

"You must be the new salesman I ordered," she'd said drily. "They didn't charge me for international shipping, so that's a plus at least!" Regina had cocked one eyebrow at him, waiting for him to acknowledge her joke about his accent.

"Ah yeah, they must have thrown that in for free," Killian had managed, before heading for his desk and catching Emma's eye on the way.

It had happened so naturally that Killian couldn't even remember thinking about walking to her desk. He'd just done it. He'd walked over, leaned over casually, stuffed a few M&Ms from her jar into his mouth, and asked,

"Is she always like that?"

"Pretty much, yeah. She used to be more stern and serious, but this past year, she's started trying to lighten up a bit. Sometimes it works and other times...well, you see."

They'd talked about what else he could expect from his co-workers, to the point where they really couldn't continue the conversation at reception, what with listening ears constantly...listening, so she'd invited him to lunch at an Italian place down the street.

"To welcome you to...whatever this place ends up being for you."

During their hour-long lunch break, Killian had learned that Mary Margaret, from accounting, was straight-laced and no-nonsense, but she had a soft spot for Killian's very own deskmate, David. David, of course, had no inkling of Mary Margaret's feelings for him. Emma's theory was that that was why he was so nasty all the time: he loved her back, but they were both too blind to see it.

He also learned that Emma was beautiful, funny, had the greatest smile he'd ever seen, and the most beautiful eyes to match. He learned that they both preferred the literary versions of anything to the film versions, that they both loved chicken parmesan and sweet potato fries, and that he would do anything to make her laugh this way all the time.

They'd gotten seats at the bar instead of a table, and they'd slowly gravitated towards each other, stools moving closer with every joke, and suddenly, right before he reached into his wallet to pay and maybe make a comment about a second date, she'd dropped the bomb.

"Oh, I should get these leftovers boxed for my boyfriend. His name's Neal, he works in the warehouse. You'll meet him soon enough."

Three long, endless years and one proposal - but no wedding, Killian hastily added to himself - and he was still here. Still gossiping with the receptionist, still leaning over her desk casually to stuff candy into his mouth.

"Are you going to Mary Margaret's bird party tonight?" she asked him.

"Wait, this party is for a _bird_? I thought it was for, like, a kid she'd never told us about or something. Surely you're joking."

"Killian. I would never joke about something as serious as a bird party. This is Archie's 3rd birthday party we're talking about."

Killian laughed, which made Emma laugh. Which made Killian's heart soar. Until the light caught off of her diamond ring and he - and his heart - crashed back down to earth.

"I do have another proposition for you though, love." It was out of his mouth before he could stop it. He wasn't one for pet names, especially for his _just friends_ , but he found himself slipping into that one with ease. Oops.

"Oh yeah? And what's that?" Her green eyes glinted with excitement - she likely expected some type of prank for David, or a revenge plan for Regina, who'd just had them waste exactly 3 hours in the conference room for a meeting about...what was it about? Regina's time-wasting meetings all blended together after a while, and Killian mostly spent his time in them laughing with Emma.

"A few of us are going out for drinks, thought maybe you'd like to come."

"Oh, yeah actually, that sounds nice! I'll ask Neal if he's okay with it."

Killian bit back a groan, nodded, and headed back to his desk.

It hadn't taken long for Killian to meet Neal, as Emma had promised. He'd come barreling in that very afternoon, only a few short hours after Killian's heart had been crushed by learning of his existence.

"You ready yet, babe? I wanna get home in time for the game."

"It's 4:45, Neal."

"Yeah, so? Hey, Gina, you're cool with Emma leaving early today, right?"

Killian turned quickly to look into the office behind him. He caught the dark flash in Regina's eyes before she grinned and agreed.

"Sure, it's been a long day, she's worked hard. We'll see you tomorrow, Emma!"

"You know she hates that nickname, Neal," she'd whispered on her way out, with a quick wave to Killian. "It was nice meeting you today!"

"You, too," but she was already gone.

Since then, Killian had tried to bond with Neal, hoping maybe he could somehow understand the relationship. Because, for the life of him, he couldn't. Where Emma was smart and creative and fun, Neal was brash and rude and just sort of boring. He never listened when Emma spoke, never supported her in her endeavors. And Killian knew this because Emma came to him to talk instead. They had a standing lunch date in the kitchen, where she'd tell him all about all of her problems - or the problems of the people on the trashy reality TV she watched.

The fact that he could so easily click with this woman, while her fiance would barely say three words to him made no sense. Killian knew he could be a bit standoffish on his bad days, but overall, he thought he was a pretty good guy. He'd had a rough go of it for a while, but he tried his best not to let it affect his daily interactions with people. He didn't know about Neal's past - didn't really want to - but he suspected that they had a bit in common, and that Neal was a version of who he could have been if he'd let the demons take him over.

Which is to say that Neal was always miserable, despite being engaged to one of the most beautiful women Killian had ever seen, and Killian did his best to keep his spirits up, despite the fact that the woman he was in love with was engaged to a total douche.

Because Killian was the person Emma went to with her problems, he knew that Neal regularly objected to workplace outings. Emma wasn't exactly a social butterfly, preferring to keep to her quiet corner of the office most of the time, but she liked to get to know people. She liked going out with her co-workers, she'd told Killian, because she had to see the business side of them, and she wanted to know what they were like when they let loose, even a little bit. But Neal was a hermit, to borrow Emma's word, and he didn't care about his own co-workers downstairs in the warehouse, nevermind Emma's co-workers up here in the land of fluorescent lights and candy jars and copy machines.

He already knew she wasn't going tonight, even before he heard her cell phone buzz and saw the disappointed look on her face.

Damn Neal.


	2. Chapter 2

In three years, Killian had learned a lot about his co-workers. He had a pretty good idea of who they were, their likes and dislikes. He knew Ruby loved gossip, mostly about celebrities, to make up for boring small town life. He knew Victor loved Ruby, but was too obsessed with himself to realize it. He knew that the girl from HR, Tracy, was a stick in the mud who almost no one liked, least of all Regina.

He knew that his deskmate, David Nolan, had a stick up his ass, and he was determined to get it out.

"David's in rare form today," he was telling Emma over lunch. The kitchen was quiet aside from the low hum of the fridge next to them.

"What's he doing now?" She took a sip of her hot chocolate, staring at him over the cup, clearly trying to hide a laugh. They had this conversation, or one similar, every week. David was _always_ in rare form. Which, Killian supposed, made it not so rare, but it did seem to be worse every week, he swore.

"I asked him about his farm, a genuine question! And-"

"A genuine question. About David's farm. Before you tell me what he said, I want to know what you asked him."

"That's...not really important."

"Killian!"

"I asked him about the sheep."

"Killian."

"I asked him if he'd ever sold any wool, Emma, it's a real question!"

She stared at him, knowing he wasn't telling the whole truth. She called it a superpower, being able to tell when people were lying to her. Killian thought there was more to it, but The Past wasn't something they talked about in all of their hours together at this table. They stuck with The Present - Neal and Regina and David, usually. Mostly Neal.

"I asked him if my friend Bo had been by to buy any wool."

"Your friend Bo." It wasn't a question. She knew he was still leaving something out.

"Yeah, you know, my good friend Bo Peep."

"KILLIAN!" She practically screeched. "Oh no, Killian, what did he say?"

"Well, he didn't catch onto the omission of the last name - not as smart as you, Swan - so he asked what my friend Bo looked like. What he would have been wearing, what day he might have shown up. The usual David line of questioning." Emma's face was bright red now, from holding in laughter. "It took him a full ten minutes to remember that he doesn't even sell wool."

She couldn't hold it in at that. She burst out laughing and Killian sat back, beaming. It was always a good lunch when she ended up in tears from laughter. The good kind of tears.

"Killian, what did he _say_!?" she asked once she'd caught her breath again.

"Well, he obviously went on about how I'd wasted his time and the time of my friend Bo, because if Bo _did_ turn up at his farm to buy wool, there wouldn't be any. And then he told me I'm a terrible friend - to Bo, of course, not to him - and also that I should really listen to people when they talk, because he's told me multiple times that he doesn't own any sheep."

"Oh, wow. A harsh lecture from Nolan today. He's serious about those sheep. Or lack thereof."

"I was thinking of setting him up."

"For a prank?"

"On a date."

"Wait, what? How did we get from sheep to dating. Unless you're setting him up with a sheep. Because that...actually might work. She might understand him better than a human woman."

"I was thinking Mary Margaret, actually."

"What?"

"You said yourself, on my very first day, that they're in love with each other. Why not set them up?" He blushed a bit, hoping she hadn't caught the fact that he remembered something so specific from their first date/not-date. He remembered every interaction with Emma, but he tried his best not to let on just how smitten he was with her.

"Because that can't be forced, Killian." She spoke like she knew from experience.

"Emma, it's been three years. And then some, if you already knew about it by then. Enough is enough. They'll both be happier for it. I'm doing it."

"Operation Prince Charming, then?"

"Why Prince Charming?"

"Because you'll need to make him into one, won't you?"

"Nah, I suspect Mary Margaret's already seen the worst of him, and she's still in love thus far."

"Fair point. Let me know how it goes," and she was gone. Killian hadn't even realized lunch was over.

Sliding back into his desk, he gave David a once-over. He was a good looking guy, just so cranky all the time. But when David glanced over at accounting, Killian saw a softness take over his features. And he was good at his job, made good money, plus he had to have a decent sized house, living on a farm and all. Mary Margaret was the stern head of accounting, head of the party planning committee, and the safety captain - whatever that meant. She was quiet, but firm, and often got what she wanted because of her dedication to whatever cause she took on. She, like David, was often cranky, but it was well-known that she wanted the best for all of her co-workers. She planned the best parties because she thought they all deserved the best.

"David, I'd like to set you up on a blind date," Killian tried not to look towards accounting, not wanting to make it obvious that she was the victim - yikes, that was harsh, he supposed.

"Is this about your friend Bo again? Killian, I'm not-"

"No, David, it's not. I just know someone I think you'd get along with. I'll set it all up, you'd just have to show up. Would that be okay with you?" He could feel Emma staring at him. He knew she hadn't thought he'd do it.

"Can I see a picture first? I have particular tastes. I doubt you'd be friends with anyone who would interest me." David crossed his arms over his chest, trying to look serious, but Killian saw his glance towards accounting.

"You'd be surprised, Dave. I think I've got a pretty good idea. We've been deskmates for years, I must have learned a thing or two by now. And no, no pictures. _Blind_ date, remember?"

"Fine. But if I don't like her, I'm leaving."

"Deal."

Killian was surprised it had been that easy to get David to agree. He knew the man didn't like him, didn't trust him. David didn't really trust anybody.

Mary Margaret was going to be much more difficult. They rarely spoke, unless there was an issue with his paychecks, so the 'I know you pretty well by now' argument wouldn't work. He was about to formulate a plan when he saw Emma get up from her desk.

"Hey, Mary Margaret? I was about to head over and get something from the vending machine, but I wanted to talk to you. Would you come with me?"

"To the vending machine?"

"Sure. It's quieter back there, so I can...ask you something."

"Fine, but let's be quick."

Emma winked at Killian as she walked by with Mary Margaret, and Killian's jaw hit the floor.

A good lass, that Swan.

Ten minutes later, he was at her desk finalizing the plans for Operation Prince Charming. They chose Ruby's grandmother's restaurant as the location - she gave Ruby's co-workers discounts, and Killian was planning to pre-pay for a bottle of champagne or something. Plus, Mary Margaret was very particular about her food, but they'd seen her eat at Granny's before, so they knew she'd get _something_. 8PM seemed like enough time for them to go home and get ready. They told their respective co-workers the plan, separately of course, not wanting to be obvious.

"Should we go and watch them from a corner booth or something?" Emma suggested.

 _Yes. We should go and sit in a corner booth and you can order your hot chocolate with cinnamon and I'll hold the door and pay and then I'll walk you to your doorstep and you'll-_

"Yeah, definitely! We'll have to be inconspicuous though!" He winked at her. "I'll pick you up at 7:30," he whispered before walking back to his desk, not giving her any time to argue.


	3. Chapter 3

"Okay, Swan, the prince is in the castle," Killian whispered to Emma. He was facing the booth David was waiting in, a tiny silver 'RESERVED' sign on the end, a bucket of ice and champagne looking awkward and out-of-place next to the bright red napkin holder. He had suggested he and Emma both sit on the same side of their table, so they could see, but she had blushed a bit and said the seat was too crowded for that, and she'd be fine over here, really. Hence, the play-by-play.

"In the castle? Really?"

"What would you like me to say, then?"

"That David's in the booth, maybe?"

"You're the one who came up with this 'Operation' title, I was just trying to stick with the theme."

She stuck her tongue out at him before looking out the window. Her eyes flashed with surprise.

"She's here!"

"Who's here?" He knew perfectly well who was there, but he wanted to see if she'd give in to his game.

She hesitated at first, thinking, taking in Mary Margaret's pale skin, short dark hair, and top button cardigan.

"Snow White is entering the kingdom," she rolled her eyes at herself, but she was smiling.

"Ha! See, Swan, it's more fun this way."

Mary Margaret walked in the door and counted booths - third one from the door, on the left-hand side, Emma had told her - before her eyes finally met David's.

Killian really didn't like his deskmate. David was too literal, didn't understand his humor, and was always bragging about his sales. It was tacky, if you asked Killian, which no one did. Killian also didn't like Mary Margaret all that much. She was judgmental and stern, and while, yes, she was the head of accounting, she was not _Killian's_ boss, but that didn't seem to stop her from telling him what to do.

But Killian _did_ like people to be happy. He liked people to be true to themselves, to their feelings, and he liked people to fall in love. He tried not to think about the fact that he hadn't been true to himself or to Emma about his feelings for her, about the unrequited love he dealt with every day.

Killian watched as Mary Margaret hesitated for a moment, before taking the final few steps and sliding into the booth. She tucked her knee length skirt under her legs, her cheeks flushing to match the pink of her cardigan. David watched her, neither of them saying anything yet. When they finally spoke, Killian was too far away to hear the words. But he could see the smiling, the blushing, and the laughter.

"Killian, what's happening?" Emma whispered, pulling him out of his thoughts.

"It worked, Swan. Chance a peek at them."

She pulled a menu over her face, blocking her from the nose down, and turned around and Killian _swore_ he heard her sigh.

"They look really happy. I'm glad you did this. Maybe they'll be nicer at work now."

"Doubtful," Killian chuckled. "But either way, they deserve each other. The good and the bad, I think. And, by the way, _we_ did this. Mary Margaret certainly wouldn't have agreed to this if I'd been the one to ask her."

They watched David and Mary Margaret for a while longer, munching on sweet potato fries all the while. And when they saw David's hand reach for Mary Margaret's over the table, they knew their work was done.

Killian stayed for a bit after Emma left, excusing herself with a few mumbled words about Neal needing dinner - the man couldn't even cook for himself, it seemed. He remained hidden behind a menu, ignoring Granny's pointed looks in his direction. She preferred her solo customers to sit at the bar stools, rather than take up one of her booths. But it was a Wednesday, nearly 10PM. She'd survive. Mary Margaret and David stood up to leave, and Killian watched them, hands intertwined, climb into the same Uber.

And still, Killian stayed, wondering why he did this to himself. He was living vicariously through them, he thought, since he couldn't find his own happy ending.

Climbing the stairs to his apartment a while later, Killian thought about how he'd found himself in Storybrooke in the first place.

He didn't like to think of himself as someone with a tragic backstory, but perhaps that's exactly what it was. He'd been orphaned at a young age, with only his brother to raise him. And Liam had been a better parent than his real parents, anyway. Well, his father at least. His mother had died before he could remember.

Liam had been Killian's absolute hero. He was strong, smart, and determined. Liam had been a high-ranking Naval officer. Liam had died saving lives.

And Killian was working at a paper company.

Just bloody fantastic.

If Killian were honest with himself, which he really did try to be, he knew that he'd found a safe, boring desk job _because_ of Liam. Not because he was frightened of meeting the same fate as Liam - although that was part of it - but because he was constantly fighting his natural instincts to follow in his older brother's footsteps. And because Liam would come back to life and kill him if he knew Killian was doing something dangerous just to live up to some imaginary bar that was never really set in the first place.

Killian worked in paper because if he left his boring, safe desk job, then he'd do something dangerous. And _that_ , more than anything, would have disappointed Liam. And Killian couldn't have that.

He looked around his apartment, at his spacious living room and meager collection of belongings. Killian wasn't much for sentimental things. He preferred his living quarters to be more open than cluttered, and so he kept things simple. He had one photo on his dresser, an old one of himself and Liam the day Liam had graduated from the Academy.

Shortly after Liam died, Killian had lost it a bit. He drowned his sorrows - nearly literally - in several bottles of rum, and only came up for air for pretty women and occasionally for a job interview. He'd always done his best to sober up and act professional, but most corporate-level employees saw through him and sent him out before the interview was even over.

Until Cora gave him a shot. He'd done a bit of traveling, crossed the pond and seen small towns and big cities and everything in between. Storybrooke was the smallest of small towns, and Killian figured he never really had a shot at one of the only big-time companies located here. Still, he went.

"Cora Mills, a pleasure," she'd taken his hand in a firm handshake - he loved a woman with a good handshake.

She'd eyed him carefully through the whole interview, comparing the disheveled mess she saw before her to the hard-working, determined young man he presented on his resume.

"You know, I can smell the rum on you. It doesn't seem like you're drunk right now, which might be _more_ worrisome considering how much rum I can smell."

"I...oh. I won't try and make excuses and waste your time, Ms. Mills. I appreciate the interview," he'd stood and gotten ready to walk out, to walk back to his car, to the flask in the glove box.

"I didn't say you had to leave. Look, Killian, I run a tight ship." Killian tried to hide his wince at her metaphor. "I expect a lot out of my employees, at every level. If I hire you on as a salesman, I'll expect just as much out of you as I do out of anyone else at this company. I see something, a fire, in you that I don't see very often - but I think you need to start believing in yourself or you'll lose that quality. I believe you can be something great. I need you to believe it, too. I'll tell you what. You've got 2 weeks. Sober up - completely, not just for the length of time of an interview - and then come back here. And then we'll talk about which of my offices you'll be a good fit for."

He couldn't believe it. This woman believed in him. No one had believed in him since Liam. He went home that afternoon and emptied every bottle of rum in his apartment, Liam watching him from the photo on the dresser in his dingy motel room. Killian knew he was imagining things, but it seemed like Liam's smile grew just a little bit that day.

He'd never expected, of course, that he'd be working under Cora's own daughter, Regina, at the home SPC office in Storybrooke itself. Or that he'd fall in love with the receptionist. Or that he'd _stay_ at SPC for so long. He'd signed a one year lease for an apartment with his first paycheck, not expecting to be there any longer. And yet….

It was meant to be a stepping stone. But somewhere along the way, he'd forgotten to move to the next stone in his path.

He fell asleep that night, thinking of his brother, sweet potato fries, hot chocolate, and how much he wished it had been himself and Emma holding hands and climbing into an Uber.


End file.
